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In most cases aerodynamics trumps weight, for sure.
A further point is that for winter bike use you want cheap and durable wheels not so much fast wheels (unless you're racing in winter then you'd still want the aero wheels for pretty much everything except hill climbs).
I mean, you could use lightweight or aero wheels during winter, sure, but then you're using nice wheels in shit weather which kind of defeats the point of a winter wheelset.
Not yet, not until I have more info. THEN I'll punish him.